Hydroxyaryl functionalized polymers

Abstract

Vulcanizates with desirable properties can be obtained from compounds incorporating polymers that include hydroxyl group-containing aryl functionalities. The functionalities can be incorporated by using any or all of appropriate initiators, monomers and optional terminating compounds. Such polymers exhibit excellent interactivity with both conventional and non-conventional fillers.

That which is claimed is: 
     
       1. A method of making a polymer that comprises terminal functionality, said method comprising
 a) providing a solution that comprises
 1) one or more ethylenically unsaturated monomers which include at least one type of polyene and 
 2) a soluble alkali metal-containing compound having the general formula R′ZQM, where
 Z is a single bond or a substituted or unsubstituted cyclic alkylene, acyclic alkylene or arylene group, 
 M is an alkali metal atom, 
 R 1  is a phenyl or polycyclic aromatic group having at least two OR 2  substituent groups where each R 2  is a group that is nonreactive toward M and capable of being hydrolyzed, and 
 Q is a group that is bonded to M through a N or Sn atom; and 
 
 
 b) allowing said alkali metal-containing compound to anionically initiate polymerization of said one or more ethylenically unsaturated monomers so as to provide a carbanionic polymer. 
 
     
     
       2. The method of  claim 1  further comprising reacting said carbanionic polymer with a compound that comprises a functionality capable of reacting with carbanionic polymers, the radical of said compound providing said polymer with a heteroatom-containing functionality. 
     
     
       3. The method of  claim 2  wherein said compound that comprises a functionality capable of reacting with carbanionic polymers further comprises an aryl group having at least one directly bonded OR group, wherein R is a hydrolyzable protecting group. 
     
     
       4. The method of  claim 3  further comprising introducing one or more active hydrogen atom-containing compounds to said solution, thereby hydrolyzing each of said at least one OR group. 
     
     
       5. The method of  claim 1  wherein two OR 2  groups are directly bonded to adjacent carbon atoms of said phenyl or polycyclic aromatic group. 
     
     
       6. The method of  claim 1  wherein Q is SnR 7   2  where each R 7  independently is a hydrocarbyl group or together form a cycloalkyl group. 
     
     
       7. The method of  claim 1  wherein Q is NR 8  where R 8  is a hydrocarbyl group. 
     
     
       8. The method of  claim 3  wherein said aryl group comprises at least two directly bonded OR groups. 
     
     
       9. The method of  claim 8  further comprising introducing one or more active hydrogen atom-containing compounds to said solution, thereby hydrolyzing each of said at least two OR groups. 
     
     
       10. The method of  claim 3  wherein two of said OR groups are directly bonded to adjacent carbon atoms of said aryl group. 
     
     
       11. The method of  claim 1  wherein two of said OR 2  groups are directly bonded to adjacent carbon atoms of said phenyl or polycyclic aromatic group. 
     
     
       12. The method of  claim 1  wherein said one or more ethylenically unsaturated monomers further comprises at least one type of vinyl aromatic compound. 
     
     
       13. The method of  claim 12  wherein said polymer comprises randomly distributed vinyl aromatic and polyene mer. 
     
     
       14. A process of making a polymer that comprises terminal functionality, said process comprising
 a) providing a solution that comprises
 1) ethylenically unsaturated monomers which include
 (A) at least one type of polyene and 
 (B) at least one type of vinyl aromatic compound, and 
 
 2) a soluble alkali metal-containing compound having the general formula R 1 ZQM, where
 Z is a single bond or a substituted or unsubstituted cyclic alkylene, acyclic alkylene or arylene group, 
 M is an alkali metal atom, 
 R 1  is a phenyl or polycyclic aromatic group having at least two OR 2  substituent groups where each R 2  is a group that is nonreactive toward M and capable of being hydrolyzed, and 
 Q is a group that is bonded to M through a N or Sn atom; 
 
 
 b) allowing said alkali metal-containing compound to anionically initiate polymerization of said one or more ethylenically unsaturated monomers so as to provide a carbanionic polymer that comprises randomly distributed vinyl aromatic and polyene mer; and 
 c) introducing one or more active hydrogen atom-containing compounds to said solution, thereby hydrolyzing each of said at least two OR 2  substituent groups and quenching said carbanionic polymer. 
 
     
     
       15. The process of  claim 14  further comprising reacting said carbanionic polymer with a compound that comprises a functionality capable of reacting with carbanionic polymers and, optionally, an aryl group having at least one directly bonded OR group where R is a hydrolyzable protecting group, the radical of said compound providing said polymer with a heteroatom-containing functionality. 
     
     
       16. The process of  claim 14  wherein two OR 2  groups are directly bonded to adjacent carbon atoms of said phenyl or polycyclic aromatic group. 
     
     
       17. The process of  claim 14  wherein Q is SnR 7   2  where each R 7  independently is a hydrocarbyl group or together form a cycloalkyl group. 
     
     
       18. The process of  claim 14  wherein Q is NR 8  where R 8  is a hydrocarbyl group.